Note that I'm single, so I can't hold property jointly. The only way I can pass real estate to an heir without probate is through a trust.

That is not true. You do not have to be married to hold property jointly. You can put anyone else on the title to your property that you want, but it is not without ramifications including that you just made a gift to that person, that property is now part of that person's assets and could be taken in a lawsuit, etc., but there is no reason you can't hold property jointly, and that can be either with rights of survivorship where the property passes to the other owner(s) upon your death or as tenants in common where each owner can sell their ownership interest separately and would leave it to whoever they want in their own will.

I hold some property with DH as JTWROS, but I have also owned a house with my brother as Tenants in Common.

I will reiterate that I think it is best to seek the advice of an estate planning attorney when doing estate planning, and not do this as DIY. There are just too many pitfalls. And yes, I could keep you entertained for hours with some pitfalls that I have seen that you would just not believe.

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